Chiral (R)- and (S)-allylic alcohols with an enantiomeric excess exceeding 99% have been prepared in good to high overall isolated yields through a two-step one-pot chemoenzymatic process based on the palladium-catalyzed Heck reaction of aryl iodides with butenone followed by an enzymatic reduction of the resultant vinylic substitution products. Alcohol dehydrogenases from Lactobacillus brevis and Thermoanaerobacter species were used to attain (R)- and (S)-stereoselectivity, respectively. (c) 2007 Elsevier Ltd. All rights reserved.
Chiral (R)- and (S)-allylic alcohols via a one-pot chemoenzymatic synthesis / Simona, Sgalla; Fabrizi, Giancarlo; Roberto, Cirilli; Macone, Alberto; Bonamore, Alessandra; Boffi, Alberto; Cacchi, Sandro. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:23(2007), pp. 2791-2796. [10.1016/j.tetasy.2007.10.043]
Chiral (R)- and (S)-allylic alcohols via a one-pot chemoenzymatic synthesis
FABRIZI, Giancarlo;MACONE, ALBERTO;BONAMORE, ALESSANDRA;BOFFI, Alberto;CACCHI, Sandro
2007
Abstract
Chiral (R)- and (S)-allylic alcohols with an enantiomeric excess exceeding 99% have been prepared in good to high overall isolated yields through a two-step one-pot chemoenzymatic process based on the palladium-catalyzed Heck reaction of aryl iodides with butenone followed by an enzymatic reduction of the resultant vinylic substitution products. Alcohol dehydrogenases from Lactobacillus brevis and Thermoanaerobacter species were used to attain (R)- and (S)-stereoselectivity, respectively. (c) 2007 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.